Director of Programs and Services - Sistering

Apr 19, 2021
Old Toronto, Ontario

Sistering is a multi-service agency for at-risk, socially isolated women and trans people in Toronto who are homeless or precariously housed. Our harm reduction philosophy is a core element of all the work we do. We operate on a trauma-informed and relationship-based model.

Our programs include a low-barrier 24/7 Drop In, Housing and Case Support, Harm Reduction, Peer Outreach, on-site Medical Clinic, On the Path to Employment and Spun Studio social enterprise. During COVID our 24/7 Drop In runs as one of the City Respite Centres, providing essential services.

Position Summary

Reporting to the Executive Director, the Director of Programs and Services is responsible for the development, implementation, management, supervision and evaluation of all the organization’s programs and services. As a member of the senior management team, the Director participates in strategic planning and budgeting initiatives in addition to problem solving. This position is also the advocacy lead, developing and connecting Sistering with advocacy initiatives benefiting Sistering participants. The Director provides direct supervision for the Drop In Manager, Case Support Manager, and other Program Coordinators.

Key Accountabilities:

Programs and Services

  • Be responsible for all facets of programming and service development and delivery, from proposal writing (in conjunction with the fund development director and program managers), through planning, budgeting, implementation, evaluation and report writing
  • Ensure high quality of comprehensive services delivery through a variety of quality assurance mechanisms
  • Lead program development and evaluation processes across the agency: ongoing review of current programs and development of new services
  • Monitor programs’ compliance with contractual agreements and grant requirements to ensure the accuracy of our reporting and that all deadlines are met
  • Ensure the implementation of ongoing data collection systems which generate information to be used in program evaluation, outcome evaluation, program reporting and funder reporting; this includes reports to funders, Board of Directors and Fundraising initiatives as well as any ad hoc reports and partner correspondence
  • Analyze trends in the services, plan and promote innovative and effective programs and community development initiatives related to street involved adult women, who have complex health issues
  • Support delivery of counseling and crisis intervention support to participants

Agency Management

  • Provide leadership in promoting the organization's anti-discrimination, anti-oppression and harm reduction efforts
  • Work with management team and Board Committees to develop and implement organizational policies, procedures, directions and initiatives
  • Develop program budget in collaboration with the Senior Leadership Team. Monitor program budgets and make adjustments as necessary. Approve program operating expenditures and reviews/approves relevant reports. Oversee and support funding requests within portfolio
  • Lead the operational and strategic planning processes and implementation
  • Ensure compliance with organizational and legal obligations
  • In the absence of the executive director, manage the day-to-day operations of the organization, including liaising with the Board of Directors as required
  • Represent the employer in union employee contract negotiations with the Union

Leadership and Supervision

  • Provide leadership, supervision and support to staff of Drop In and other Program Teams
  • Supervise and ensure performance management of Drop In Manager, Case Support Manager, and other Program Coordinators. Identify goals and benchmarks for professional development and/or improvement of program managers and coordinators
  • Facilitate program services meetings and arrange for and/or facilitate in-service training for staff
  • Participate in the recruitment, hiring, ongoing supervision, performance management and disciplinary action of managers, coordinators and staff


  • Liaise and collaborate with external groups/agencies, strengthen and build partnerships with other organizations aimed at fostering the development of collaborative projects
  • Ensure Sistering’s active participation in initiatives and coalitions, supporting Sistering’s mission and goals
  • Develop opportunities for new funding streams and contracts within the community including local, regional and federal government entities in partnership with Executive Director and Fund Development Director
  • Provide leadership and support to staff and Board in the development and implementation of advocacy goals and objectives

Other Related Duties

  • Attend Board meetings as necessary to educate Board members about agency programs, community needs and program recommendations
  • Provide outcomes and evaluation reports to the Board and Committees on the impact of the agency’s programs and services as required by the Executive Director
  • Participate on key board committees as appropriate

Education, Qualifications and Experience:

  • Degree in social work, sociology, health sciences or comparable field
  • A minimum of five years of proven experience in a leadership capacity in the community based non-profit sector preferably with a focus on homelessness services
  • Policy expertise in the areas of homelessness and housing, harm reduction and/or peer programming
  • Experience of leadership and proven track record of leading change management projects or initiatives in a unionized environment
  • Experience and a proven track record in strategic planning, budget management, business development and politically astute
  • Strong understanding of and working experience with an anti-oppression and anti-racism framework
  • Strong conflict resolution skills
  • Experience in training, mentoring and coaching in a team setting; commitment to employee engagement and leadership development at all levels
  • Strong skills in performance management, evaluation and improvement
  • Exceptional interpersonal and presentation skills
  • Excellent written and oral communication skills

Work Conditions: 

This position may be required to work some evenings and weekends and be on a roster for on-call support.

This position works in the office and community. Sistering is a 24/7 operation, fast paced, intense environment. There may be the risk of exposure to potentially unpredictable behaviours and situations. Sistering is a pet friendly facility and as such, employees will be expected to be in the proximity of animals.


  • Competitive salary based on experience
  • Excellent benefits package
  • Four paid personal days off annually

How To Apply:

Please send cover letter and resume in ONE file to, specifying “Director Application” in the subject line.

Sistering is an Equal Opportunity Employer; we welcome and encourage applications from racialized persons/visible minorities, Indigenous persons, persons with disabilities, ethnic minorities, and persons of minority sexual orientations and gender identities.

Persons with disabilities who anticipate needing accommodations for any part of the application process please contact, in confidence, Tina Cai, Human Resources Manager, by email, or phone at 416-926-9762 ext. 242

This job is from CharityVillage
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